You're not thinking strategically-slash-cynically enough.
This guy did the "show up and try" thing, which he then parlayed into the title of Official White House Tech Fixer. That's the sort of résumé-enhancing title that will bring you literally as much money as you want for the rest of your natural life.
What can you do with it? Do your stint in government, then hang out your shingle as a private consultant. That very day, Fortune 500s will start pointing firehoses spewing money at you in exchange for "consultations" where you parachute in to tell them all their problems are due to their IT staff being idiots. Your White House title will give you unimpeachable (heh) credibility in their eyes. This credibility will last for decades, long after your specific tech knowledge has become obsolete, and will draw you business regardless of political affiliation. (CEOs don't follow politics, all they know is that you're Trusted By Big Shots.) You will also be invited to places like Davos and TED to wax rhapsodic on the Importance of Technology, further prolonging your marketability. It's a meal ticket for life.
It's possible that Mr. Dickerson was financially secure enough already that he didn't need the future payout this title will bring. If anything, that just argues more that such an opportunity would be better for someone who hasn't already made their pile, because for that person, such an opportunity is how a pile is made. Trading a little present-day income for a huge payout down the line is a career approach that should be familiar to those who work in and around VC-backed startups.
Of course, the problem with this strategy is that it only really works best for the first person to pull it off. Everyone after that gets less luster from their association; there will be many Tech Fixers who will come out of programs like the USDS, but none as prominent as the original Fixer. It's a risk/reward thing -- it was not obvious when Mr. Dickerson tried it that "showing up and trying" could lead to glory; so when he tried it, and it worked, he didn't have to share the glory with an army of others. Now it is obvious, so lots of people will pile on to try doing it themselves, and they'll divide the prestige between them. So it goes.